2-iodoethylcyclopropane

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Triphenylphosphine (2.86 g, 10.9 mmol) was added to a solution of (2-iodoethyl)cyclopropane obtained (2.14 g, 10.9 mmol) in acetonitrile (5 mL), and the mixture was heated to reflux for 15 hr. After cooling, diethyl ether was added thereto and a precipitaed solid was collected by filtration to afford (2-cyclopropylethyl)(triphenyl)phosphonium iodide as a colorless powder (3.87 g). the mixture was heated to reflux for 15 hr After cooling a precipitaed solid was collected by filtration

反応条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred solution of 1-cyclopropyl-2-iodoethane (12.5 g, 63.9 mmol, 5 equiv) in anhydrous Et2O (128 mL) at −78° C. was added tert-butyl lithium (1.7M in pentane, 75 mL, 128 mmol, 10 equiv). The resulting white suspension was stirred at −78° C. for 50 min and added via cannula to a suspension of 7 (3.83 g, 12.8 mmol) in THF (64 mL) at −78° C. The resulting dark yellow mixture was stirred at −78° C. for 30 min and then allowed to warm to 0° C. over 5 h. The reaction was quenched with satd. NH4Cl (100 mL) and H2O (100 mL). The reaction mixture was extracted with EtOAc (3×100 mL) and the combined organic layers washed with brine and dried (MgSO4). Chromatography (SiO2, 40 to 50% EtOAc-hexane) provided the desired product as a yellow solid (2.92 g, 62%). ESI HRMS m/z 370.1735 (M++H, C17H16ClF3N3O requires 370.0934). The resulting dark yellow mixture was stirred at −78° C. for 30 min to warm to 0° C. over 5 h The reaction was quenched with satd The reaction mixture was extracted with EtOAc (3×100 mL) the combined organic layers washed with brine dried (MgSO4)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Analogously to general procedure (I) N-(3,3-dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide (4 g) is alkylated using (2-iodo-ethyl)-cyclopropane (5.36 g; 27.3 mmol) and K2CO3 (6.30 g; 45.6 mmol) at 55° C. for 12 h. After aqueous work-up the crude material (4.21 g) is de-acetylated in hydrochloric acid (6 N, 30 ml) at reflux. After aqueous work-up 5-amino-1-(2-cyclopropyl-ethyl)-3,3-dimethyl-6-nitro-1,3-dihydro-indol-2-one (3.75 g) is obtained and used without further purification. at 55° C. for 12 h at reflux

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Analogously to general procedure (I) N-(3,3-dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide (4 g) is alkylated using (2-iodo-ethyl)-cyclopropane (5.36 g; 27.3 mmol) and K2CO3 (6.30 g; 45.6 mmol) at 55° C. for 12 h. After aqueous work-up the crude material (4.21 g) is de-acetylated in hydrochloric acid (6 N, 30 ml) at reflux. After aqueous work-up 5-amino-1-(2-cyclopropyl-ethyl)-3,3-dimethyl-6-nitro-1,3-dihydro-indol-2-one (3.75 g) is obtained and used without further purification. at 55° C. for 12 h at reflux

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Analogously to general procedure (I) N-(3,3-dimethyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide (4 g) is alkylated using (2-iodo-ethyl)-cyclopropane (5.36 g; 27.3 mmol) and K2CO3 (6.30 g; 45.6 mmol) at 55° C. for 12 h. After aqueous work-up the crude material (4.21 g) is de-acetylated in hydrochloric acid (6 N, 30 ml) at reflux. After aqueous work-up 5-amino-1-(2-cyclopropyl-ethyl)-3,3-dimethyl-6-nitro-1,3-dihydro-indol-2-one (3.75 g) is obtained and used without further purification. at 55° C. for 12 h at reflux

反応条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred solution of 1-cyclopropyl-2-iodoethane (12.5g, 63.9 mmol, 5 equiv) in anhydrous Et2O (128 mL) at −78° C. was added tert-butyl lithium (1.7M in pentane, 75 mL, 128 mmol, 10 equiv). The resulting white suspension was stirred at −78° C. for 50 min and added via cannula to a suspension of 7 (3.83 g, 12.8 mmol) in THF (64 mL) at −78° C. The resulting dark yellow mixture was stirred at −78° C. for 30 min and then allowed to warm to 0° C. over 5 h. The reaction was quenched with satd. NH4Cl (100 mL) and H2O (100 mL). The reaction mixture was extracted with EtOAc (3×100 mL) and the combined organic layers washed with brine and dried (MgSO4). Chromatography (SiO2, 40 to 50% EtOAc-hexane) provided the desired product as a yellow solid (2.92 g, 62%). ESI HRMS m/z 370.1735 (M++H, C17H16ClF3N3O requires 370.0934). The resulting dark yellow mixture was stirred at −78° C. for 30 min to warm to 0° C. over 5 h The reaction was quenched with satd The reaction mixture was extracted with EtOAc (3×100 mL) the combined organic layers washed with brine dried (MgSO4)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Triphenylphosphine (2.86 g, 10.9 mmol) was added to a solution of (2-iodoethyl)cyclopropane obtained (2.14 g, 10.9 mmol) in acetonitrile (5 mL), and the mixture was heated to reflux for 15 hr. After cooling, diethyl ether was added thereto and a precipitaed solid was collected by filtration to afford (2-cyclopropylethyl)(triphenyl)phosphonium iodide as a colorless powder (3.87 g). the mixture was heated to reflux for 15 hr After cooling a precipitaed solid was collected by filtration

反応条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred solution of 1-cyclopropyl-2-iodoethane (12.5 g, 63.9 mmol, 5 equiv) in anhydrous Et2O (128 mL) at −78° C. was added tert-butyl lithium (1.7M in pentane, 75 mL, 128 mmol, 10 equiv). The resulting white suspension was stirred at −78° C. for 50 min and added via cannula to a suspension of 7 (3.83 g, 12.8 mmol) in THF (64 mL) at −78° C. The resulting dark yellow mixture was stirred at −78° C. for 30 min and then allowed to warm to 0° C. over 5 h. The reaction was quenched with satd. NH4Cl (100 mL) and H2O (100 mL). The reaction mixture was extracted with EtOAc (3×100 mL) and the combined organic layers washed with brine and dried (MgSO4). Chromatography (SiO2, 40 to 50% EtOAc-hexane) provided the desired product as a yellow solid (2.92 g, 62%). ESI HRMS m/z 370.1735 (M++H, C17H16ClF3N3O requires 370.0934). The resulting dark yellow mixture was stirred at −78° C. for 30 min to warm to 0° C. over 5 h The reaction was quenched with satd The reaction mixture was extracted with EtOAc (3×100 mL) the combined organic layers washed with brine dried (MgSO4)